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1.  4-(4-Chloro­phen­yl)-2,6-bis­(1H-indol-3-yl)-1,4-dihydro­pyridine-3,5-dicarbo­nitrile ethanol monosolvate 
In the title compound, C29H18ClN5·C2H6O, the dihydro­pyridine ring adopts a strongly flattened envelope conformation, with a maximum deviation of 0.139 (2) Å from its best plane for the Csp 3 atom. The dihedral angles between the dihydro­pyridine ring plane and the two indole rings in positions 2 and 6 are 34.28 (5) and 40.50 (6)°, respectively. In turn, the benzene ring and the dihydro­pyridine ring are oriented at a dihedral angle of 74.69 (6)°. An intra­molecular C—H⋯Cl hydrogen bond occurs. In the crystal, mol­ecules are linked by N—H⋯N, N—H⋯O and O—H⋯N hydrogen bonds into layers parallel to (001). There are short C—H⋯Cl contacts between mol­ecules in neighboring layers.
doi:10.1107/S1600536812013906
PMCID: PMC3344446  PMID: 22590208
2.  Diethyl 4-[2-(4-meth­oxy­phen­yl)-1H-pyrazol-3-yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C23H27N3O5, the pyrazole ring is inclined at dihedral angles of 38.16 (6) and 80.80 (6)°, respectively, to the least-squares planes of the benzene and dihydro­pyridine rings. In the crystal, adjacent mol­ecules are linked via a pair of N—H⋯N hydrogen bonds, forming an inversion dimer. The dimers are stacked in a column along the a axis through N—H⋯O hydrogen bonds. Intra- and inter­molecular C—H⋯N and C—H⋯O hydrogen bonds are also observed.
doi:10.1107/S1600536811017600
PMCID: PMC3120286  PMID: 21754799
3.  1,1′-[4-(2,4-Dichloro­phen­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­yl]diethanone 
In the title compound, C17H17Cl2NO2, the central 1,4-dihydro­pyridine ring adopts a flattened-boat conformation. The ethanone substituents of the dihydro­pyridine ring at positions 3 and 5 have synperiplanar (cis) or anti­periplanar (trans) conformations with respect to the adjacent C=C bonds in the dihydro­pyridine ring. The 2,4-dichloro­phenyl ring is almost planar [r.m.s. deviation = 0.0045 (1) Å] and almost perpendicular [89.27 (3)°] to the mean plane of the dihydro­pyridine ring. In the crystal, an N—H⋯O hydrogen bond links mol­ecules into a zigzag chain along the ac diagonal. C—H⋯Cl contacts form centrosymmetric dimers and additional weak C—H⋯O contacts further consolidate the packing.
doi:10.1107/S1600536810052839
PMCID: PMC3051630  PMID: 21523057
4.  9-(3-Bromo-5-chloro-2-hy­droxy­phen­yl)-10-(2-hy­droxy­eth­yl)-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione 
In the title compound, C21H21BrClNO4, the dihydro­pyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hy­droxy­phenyl ring forms a dihedral angles of 84.44 (7)° with the dihydro­pyridine mean plane. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond, with an S(8) ring motif. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional network.
doi:10.1107/S1600536812050222
PMCID: PMC3588342  PMID: 23476467
5.  Dimethyl 4-[3-(4-meth­oxy­phen­yl)-1-phenyl-1H-pyrazol-4-yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate dihydrate 
In the title compound, C27H27N3O5·2H2O, the dihydro­pyridine ring adopts a flattened boat conformation. The central pyrazole ring is essentially planar [maximum deviation of 0.003 (1) Å] and makes dihedral angles of 50.42 (6) and 26.44 (6)° with the benzene rings. In the crystal, mol­ecules are linked via N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds into two-dimensional networks parallel to the bc plane. The crystal structure is further consolidated by weak C—H⋯π inter­actions.
doi:10.1107/S1600536812027936
PMCID: PMC3394006  PMID: 22798871
6.  Diethyl 2,6-dimethyl-4-(5-phenyl-1H-pyrazol-4-yl)-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C22H25N3O4, the dihydro­pyridine ring adopts a flattened boat conformation. The pyrazole ring makes a dihedral angle of 29.04 (5)° with the benzene ring. The mol­ecular structure is stabilized by an intra­molecular C—H⋯O hydrogen bond which generates an S(9) ring motif. In the crystal, mol­ecules are linked via N—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ab plane. The crystal structure is further consolidated by weak C—H⋯π inter­actions.
doi:10.1107/S1600536812008173
PMCID: PMC3297939  PMID: 22412742
7.  3-[5-(4-Chloro­phen­yl)-1-(4-methoxy­phen­yl)-1H-pyrazol-3-yl]propionic acid and the corresponding methyl ester 
The synthesis of 3-[5-(4-chloro­phen­yl)-1-(4-methoxy­phen­yl)-1H-pyrazol-3-yl]propionic acid, C19H17ClN2O3, (I), and its corresponding methyl ester, methyl 3-[5-(4-chloro­phen­yl)-1-(4-methoxy­phen­yl)-1H-pyrazol-3-yl]propionate, C20H19ClN2O3, (II), is regiospecific. However, correct identification of the regioisomer formed by spectroscopic techniques is not trivial and single-crystal X-ray analysis provided the only means of unambiguous structure determination. Compound (I) crystallizes with Z′ = 2. The propionic acid groups of the two crystallographically unique mol­ecules form a hydrogen-bonded dimer, as is typical of carboxylic acid groups in the solid state. Conformational differences between the meth­oxy­benzene and pyrazole rings give rise to two unique mol­ecules. The structure of (II) features just one mol­ecule in the asymmetric unit and the crystal packing makes greater use than (I) of weak C—H⋯A inter­actions, despite the lack of any functional groups for classical hydrogen bonding.
doi:10.1107/S010827010900941X
PMCID: PMC2724994  PMID: 19346614
8.  Dimethyl 4-(4-formyl­phen­yl)-2,6-di­methyl-1,4-dihydro­pyridine-3,5-dicar­boxyl­ate 
The title compound, C18H19NO5, is a product of the Hantzsch reaction of p-phthalaldehyde, methyl acetoacetate, and ammonium acetate. The 1,4-dihydro­pyridine ring of the mol­ecule adopts a flattened boat conformation. The benzene ring is almost perpendicular to the 1,4-dihydro­pyridine ring; the plane through the six C atoms of the benzene ring and the plane through the four C atoms that form the base of the boat-shaped 1,4-dihydro­pyridine ring (excluding the ring N atom and the opposite ring C atom) make a dihedral angle of 87.60 (3)°. Inter­molecular N—H⋯O hydrogen bonds result in the formation of extended chains along the a axis.
doi:10.1107/S1600536807063428
PMCID: PMC2915344  PMID: 21200858
9.  N-[2-({[1-(4-Chloro­phen­yl)-1H-pyrazol-3-yl]­oxy}meth­yl)phen­yl]-N-meth­oxy­hydrazinecarboxamide 
In the title compound, C18H18ClN5O3, the hydrazinecarboxamide N—N—C(O)—N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chloro­phenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers that are further linked into chains along the a-axis direction by N—H⋯N hydrogen bonds. In addition, π–π stacking inter­actions are observed between benzene rings [centroid–centroid distance = 3.680 (1) Å].
doi:10.1107/S1600536812038214
PMCID: PMC3470263  PMID: 23125707
10.  (4-Chloro­phen­yl)[1-(4-methoxy­phen­yl)-3-(5-nitro-2-fur­yl)-1H-pyrazol-4-yl]methanone 
In the title compound, C21H14ClN3O5, an intra­molecular C—H⋯O hydrogen bond generates an S(7) ring motif and the furan and pyrazole rings are almost coplanar, making a dihedral angle of 1.98 (5)°. The pyrazole ring is inclined at dihedral angles of 47.59 (4) and 7.27 (4)° to the chloro­phenyl and methoxy­phenyl groups, respectively. The nitro group is almost coplanar to its attached furan ring [dihedral angle = 2.03 (12)°]. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The crystal structure also features short inter­molecular O⋯N [2.8546 (12) Å] and Cl⋯O [3.0844 (9) Å] contacts as well as aromatic π–π stacking inter­actions [centroid–centroid distance = 3.4367 (6) Å].
doi:10.1107/S1600536810011931
PMCID: PMC2979246  PMID: 21579120
11.  Diethyl 4-(2,4-dichloro­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C19H21Cl2NO4, the dihydro­pyridine ring adopts a flattened boat conformation. The dichloro­phenyl ring is oriented almost perpendicular to the planar part of the dihydro­pyridine ring [dihedral angle = 89.1 (1)°]. An intra­molecular C—H⋯O hydrogen bond is observed. In the crystal structure, mol­ecules are linked into chains along the b axis by N—H⋯O hydrogen bonds
doi:10.1107/S1600536810001066
PMCID: PMC2979797  PMID: 21579787
12.  Dimethyl 4-(4-ethoxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title mol­ecule, C19H23NO5, the dihedral angle formed by the benzene ring and the planar part of the dihydro­pyridine ring is 83.52 (5)°. The dihydro­pyridine ring adopts a flattened boat conformation. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, generating chains running parallel to [100]. The crystal structure is consolidated by C—H⋯O contacts.
doi:10.1107/S1600536809033364
PMCID: PMC2969859  PMID: 21577652
13.  (Z)-1-(2-Chloro­phen­yl)-3-methyl-4-[2-(4-nitro­phen­yl)hydrazin-1-yl­idene]-1H-pyrazol-5(4H)-one 
There are two independent mol­ecules, A and B, in the asymmetric unit of the title compound, C16H12ClN5O3. The relative orientations of the chloro­phenyl ring with respect to the pyrazole ring in the two crystallographically independent mol­ecules are different, and their corresponding dihedral angles are −53.3 (2) and 114.09 (18)° in mol­ecules A and B, respectively. There are two strong intramolecular N—H⋯O hydrogen bonds, and two weak intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds. The crystal packing is constructed by weak C—H⋯O and N—H⋯O inter­actions, and two π–π stacking inter­actions [centroid–centroid distances = 3.7894 (9) and 3.5719 (10) Å], forming a mol­ecular ladder along the a axis.
doi:10.1107/S1600536812029790
PMCID: PMC3414286  PMID: 22904819
14.  Crystal structure of (3,5-di­chloro-2-hy­droxy­phen­yl){1-[(naphthalen-1-yl)carbon­yl]-1H-pyrazol-4-yl}methanone 
The title compound is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. In the crystal, mol­ecules are linked through stacking inter­actions between the pyrazole rings and between the naphthalene and phenyl rings, and through inter­molecular C—H⋯O hydrogen bonds to form inversion dimers.
The title compound, C21H12Cl2N2O3, is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. The dihedral angles between the naphthalene ring system and the pyrazole ring, the pyrazole and phenyl rings and the naphthalene ring system and the phenyl ring are 49.44 (13), 49.87 (16) and 0.58 (11)°, respectively. The phenolic proton forms an intra­molecular O—H⋯O hydrogen bond with an adjacent carbonyl O atom. In the crystal, the mol­ecules are linked through stacking inter­actions between the pyrazole rings [centroid–centroid distances = 3.546 (3)] and between the naphthalene ring system and the phenyl ring [centroid–centroid distances = 3.609 (4) Å] along the a-axis direction. The mol­ecules are further connected through C—H⋯O hydrogen bonds, forming inversion dimers.
doi:10.1107/S1600536814024684
PMCID: PMC4257447  PMID: 25552982
crystal structure; diaroyl pyrazole; cyclization; stacking inter­action; C—H⋯O hydrogen bonding
15.  Dimethyl 4-(4-hy­droxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
The title mol­ecule, C17H19NO5, was prepared by a Hantzsch dihydro­pyridine synthesis from 4-hy­droxy­benzaldehyde, methyl acetoacetate and NH4HCO3. In the mol­ecular structure of the title compound, the dihydro­pyridine ring adopts a flattened boat conformation and the plane of the base of the boat forms a dihedral angle of 80.8 (2)° with the aromatic six-membered ring. The packing is stabilized by strong inter­molecular N—H⋯Ocarbon­yl, Ohydrox­y—H⋯Ocarbon­yl and weak intra­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811032521
PMCID: PMC3200733  PMID: 22064645
16.  Dimethyl 4-(3,4-dimethoxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C19H23NO6, the 1,4-dihydro­pyridine ring is twisted slightly from planarity, with a maximum deviation of 0.101 (1) Å, and adopts a very flattened boat conformation. The dihedral angle formed between the plane through the four C atoms of the 1,4-dihydro­pyridine ring and the benzene ring is 84.67 (7)°. In the crystal structure, inter­molecular N—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network.
doi:10.1107/S160053681001679X
PMCID: PMC2979474  PMID: 21579441
17.  Diethyl 4-[4-(dimethyl­amino)phen­yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C21H28N2O4, the dihydro­pyridine ring adopts a flattened boat conformation. The mean plane of the dihydro­pyridine ring and the attached benzene ring form a dihedral angle of 85.1 (1) Å. One of two ethyl fragments is disordered between two conformations in a 0.67 (4):0.33 (4) ratio. In the crystal structure, mol­ecules related by translation along the a axis are linked into chains via inter­molecular N—H⋯O hydrogen bonds.
doi:10.1107/S1600536810003508
PMCID: PMC2983663  PMID: 21580293
18.  Diisobutyl 4-(3-eth­oxy-4-hy­droxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
The asymmetric unit of the title compound, C25H35NO6, contains two independent mol­ecules. In each mol­ecule, the 1,4-dihydro­pyridine ring adopts a flattened boat conformation. The dihedral angles between the 1,4-dihydro­pyridine and benzene rings are 87.55 (7) and 87.23 (7)°. In one of these mol­ecules, one of the isobutyl groups is disordered over two sets of sites, with an occupancy ratio of 0.890 (2):0.110 (2). In the crystal, mol­ecules are linked through N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds forming two-dimensional networks parallel to the ab plane. The crystal structure is further stabilized by weak C—H⋯π inter­actions.
doi:10.1107/S1600536811055334
PMCID: PMC3274982  PMID: 22346927
19.  Dimethyl 2,6-dimethyl-4-(3-phenyl-1H-pyrazol-4-yl)-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C20H21N3O4, the 1,4-dihydro­pyridine ring adopts a boat conformation. An intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif. The pyrazole ring makes dihedral angles of 87.81 (7) and 45.09 (7)° with the mean plane of the 1,4-dihydro­pyridine ring and the phenyl ring, respectively. In the crystal, mol­ecules are linked by N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds into a three-dimensional network.
doi:10.1107/S1600536812008306
PMCID: PMC3343908  PMID: 22589989
20.  Ethyl 6-amino-8-(4-chloro­phen­yl)-9-nitro-2,3,4,8-tetra­hydro­pyrido[2,1-b][1,3]thia­zine-7-carboxyl­ate 
In the structure of the title compound, C17H18ClN3O4S, the thia­zinane ring displays a twist-boat conformation. The 1,4-dihydro­pyridine ring is approximately perpendicular to the benzene ring [dihedral angle = 88.3 (1)°]. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by N—H⋯O inter­actions into a C(8) chain along [100].
doi:10.1107/S1600536811032193
PMCID: PMC3200856  PMID: 22058968
21.  4-{2-[2-(4-Chloro­benzyl­idene)hydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-(4-meth­oxy­phen­yl)sydnone 
The title compound, C19H15ClN6O3S, exists in trans and cis configurations with respect to the acyclic C=N bonds. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.013 (1) Å] and forms dihedral angles of 34.76 (4) and 48.67 (4)° with the benzene rings. An intra­molecular C—H⋯O hydrogen bond stabilizes the mol­ecular structure and forms an S(6) ring motif. In the crystal packing, inter­molecular N—H⋯N hydrogen bonds link centrosymmetrically related mol­ecules into dimers, generating R 2 2(8) ring motifs. The dimers are then linked into a three-dimensional network by inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds, and by C—H⋯π inter­actions. Further stabilization is provided by π–π inter­actions involving the sydnone rings, with centroid–centroid separations of 3.4198 (5) Å.
doi:10.1107/S1600536811013900
PMCID: PMC3089192  PMID: 21754480
22.  3-Bromo-1-(3-chloro­pyridin-2-yl)-N-(4-eth­oxy­phen­yl)-1H-pyrazole-5-carbox­amide 
In the title compound, C17H14BrClN4O2, the pyrazole ring is almost coplanar with the benzene ring [dihedral angle = 0.5 (2)°], whereas the pyrazole ring is close to perpendicular to the 3-chloro­pyridine ring [dihedral angle = 73.7 (2)°]. An intra­molecular C—H⋯O hydrogen bond occurs. The dominant inter­action in the crystal packing is an N—H⋯N hydrogen bond, which generates a chain along the c axis. Weak inter­molecular C—H⋯O and C—H⋯N contacts are also observed
doi:10.1107/S1600536810040158
PMCID: PMC3009256  PMID: 21589129
23.  1-[5-Acetyl-4-(4-bromo­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridin-3-yl]ethanone monohydrate 
The 1,4-dihydro­pyridine ring in the title hydrate, C17H18BrNO2·H2O, has a flattened-boat conformation, and the benzene ring is occupies a position orthogonal to this [dihedral angle: 82.19 (16)°]. In the crystal packing, supra­molecular arrays mediated by N—H⋯Owater and Owater—H⋯Ocarbon­yl hydrogen bonding are formed in the bc plane. A highly disordered solvent mol­ecule is present within a mol­ecular cavity defined by the organic and water mol­ecules. Its contribution to the electron density was removed from the observed data in the final cycles of refinement and the formula, mol­ecular weight and density are given without taking into account the contribution of the solvent mol­ecule.
doi:10.1107/S1600536810006124
PMCID: PMC2983612  PMID: 21580408
24.  Crystal structure of 9-(3-bromo-5-chloro-2-hydroxy­phen­yl)-10-(2-hy­droxy­eth­yl)-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione 
The structure of a hydroacridine with significant pharmaceutical potential is reported. The acridinone ring system is in the shape of a shallow V with the majority of the ring system substituents on its convex surface; a plethora of classical and non-classical hydrogen bonds stack the molecules into interconnected columns.
The title compound C25H29BrClNO4, comprises a 3,3,6,6-tetra­methyl­tetra­hydro­acridine-1,8-dione ring system that carries a hy­droxy­ethyl substituent on the acridine N atom and a 3-bromo-5-chloro-2-hy­droxy­phenyl ring on the central methine C atom of the di­hydro­pyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 89.84 (6)° and this conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond between the hy­droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. In the crystal, O—H⋯O, C—H⋯O and C—H⋯Br hydrogen bonds combine to stack mol­ecules in inter­connected columns propagating along the a-axis direction.
doi:10.1107/S1600536814009556
PMCID: PMC4158539  PMID: 25249850
crystal structure; acridine; hydro­acridine
25.  Diethyl 2,6-dimethyl-4-[4-(3-phenyl­acrylo­yloxy)phen­yl]-1,4-dihydro­pyridine-3,5-dicarboxyl­ate hemihydrate 
In the title ester derivative, C28H29NO6·0.5H2O, the 1,4-dihydro­pyridine ring has a flattened boat conformation. The mean plane is almost perpendicular to the attached benzene ring, making a dihedral angle of 86.87 (9)°. The terminal phenyl ring is inclined to the central benzene ring by 67.56 (12)°. In the crystal, mol­ecules are bridged via O—H⋯O hydrogen bonds involving the partially occupied water mol­ecule, and this arrangement is strengthened by a pair of N—H⋯O hydrogen bonds and C—H⋯O inter­actions. The ethyl atoms of one of the ethyl ester groups are disordered over two sites with an occupancy ratio of 0.716 (5):0.284 (5).
doi:10.1107/S1600536813004108
PMCID: PMC3588479  PMID: 23476574

Results 1-25 (109908)